The First Five Times
by LifeIChose
Summary: The first five times Blair and Dan hook up.


**A/N:** This is what happens when I'm bored and listening to music.

Title and lyrics in italics come from Stars.

* * *

><p><em>The first time, in your backyard<br>Underneath the plastic sheeting  
>Outside, it was pouring<br>And we were drunk as shit_

_XXX  
><em>

He can barely remember the first time.

He wakes up next to Blair with a hangover unlike one he has ever experienced. He shakes the brunette next to him up. When her eyes finally open and she takes in the boy next to her, she bolts up, her eyes as wide as her movements are quick.

"I'm sure it's not what it looks like," he tries to say.

She covers her mouth with her hand and runs to the bathroom.

He can hear her emptying her stomach despite the tap she has turned on.

It is less than romantic.

* * *

><p>It starts with so-called accidents: running into each other at foreign films and museums.<p>

It grows into an accidental friendship until he proposes it could be something more. She agrees to test the theory but their lips hardly touch before she is pushing away though she is the one who pulled him in.

"I can't do it, Humphrey," she declares, taking a step away from him. "You, me…" She shudders.

Dan feels simultaneously sad, insulted and relieved.

Chuck and Serena walk in a few minutes later and the way Chuck is looking at Blair unsettles Dan.

The relief floods him then, overpowering every other emotion.

As Serena drags him from the couple, he realizes he felt something. He did not need a kiss to prove it. But Blair is still so caught up in Chuck that she could never feel anything real for him.

If he had kissed her, it would have been the end of his world, as he knew it.

He lets Serena lead him away.

* * *

><p>They stay friends, not on purpose, it just happens.<p>

Because his family is falling apart and because he misses her, it is so hard to pretend that he still can't tolerate her when she comes around to visit Serena who is supporting her Mother, so he doesn't.

She lets him because it should be easier this time with Chuck and it's just not, and she wants to be there for Serena, and she hates it but she misses him.

So they stay friends, real friends, not accidental ones and when summer comes and everyone including Chuck leaves, she ditches her summer internship plans, decides to pull a Serena and hang out in the Hamptons all summer and invites him to come along.

On their second to last day in the Hamptons, she reads of Chuck's engagement to Raina on Gossip Girl. She calls Nate who was supposed to be in Europe with Raina.

Her calls go unanswered and she can't put it past Chuck that this would be true.

"What can I do?" Dan asks with his kind brown eyes and understanding voice.

She unscrews Eleanor's fine whisky. "Drink to me."

Her voice is hard but her eyes are dewy.

He matches her shot for shot.

* * *

><p>She silences him when he asks to talk about it.<p>

"I'll see you," she says as she closes her Manhattan door in his face.

The Hamptons seems so far away.

He goes back to Brooklyn with faint memories of soft lips devouring his. He may not remember much but he remembers feeling good.

* * *

><p><em>Next time, at a party<br>When all our friends were there_

_XXX  
><em>

End of summer comes with welcome back parties.

He agonizes whether to go to Lily's. He is sure that Blair will be there. He is not so sure as to whether that it is a good or bad thing.

Blair is there. So are Chuck and Raina. But so is Nate.

He watches the drama unfold from the outskirts.

Gossip Girl got her facts wrongs. Nate is engaged to Raina. Chuck as usual is back to being in love with Blair.

Dan watches them do their usual dance and heads to the bar. Downing his drink, he looks around the room for Blair but doesn't spot her.

He goes off in search of her but doesn't get far. She pulls him into a room and her lips are on his before he can speak.

"Is this about Chuck?" he tries to ask but his words are muffled by her persistent lips.

He stops fighting it when her fingers slip deep into his hair, her whole body arching into his.

* * *

><p>"I have to go," she says even as her lips find his again.<p>

"Should we talk about this?" he asks, ever so serious.

"Why ruin the fun?" she counters with a teasing smile and a raised brow.

He holds her gaze in a silent duel. He is well aware of her belief that if something is not voiced out loud, it makes it less real.

She breaks first, lowering her gaze before heading to the door.

He lets her leave and he is sure she takes his heart with him.

He knew he couldn't kiss her without falling in love.

* * *

><p><em>The third time, in the doorway<br>Lights all on around us  
>And the audience beside us<em>

_XXX  
><em>

Serena comes back later than most, in mid September, and insists on throwing a party for herself.

Summer is always good for Serena. She is tanned skin and shining eyes. She seems happy.

Dan sips on a beer and feels a headache coming on. It's not an early hangover but general annoyance at the crowd around him.

He watches Nate and Raina smiling sweetly at each other and feels nauseous. Serena seems too bright and Chuck chasing Blair is the cherry on top of a shitty cake. He has seen the routine so many times. Everyone knows how the story will end.

Except he's wrong. Because as he abandons his beer and heads to the door sure that no one will notice, Blair comes chasing after him.

"What?" he asks with the impatience he used to have in voice for her when he thought of her as just a spoiled Upper East Side Princess.

She recoils and he softens. "I'm sorry but I can't do this."

"I'm not trying to hurt you," she says.

He shrugs. "But you are. You can't treat me like one of your minions, someone you can just use and dismiss."

Her lips curl up and he is sure she is going to retort with a comment about how she would never kiss one of her minions but she surprises him yet again. "I know."

"So what now?"

"I don't know," she answers.

He is not sure either but her answer is just not good enough.

He turns to leave but she yet again stops him, this time with her hand on his retreating arm.

"Blair," he sighs tiredly as he turns to face her.

"I'm not trying to hurt you," she repeats in a small voice. "I just-"

She looks so tiny and vulnerable and it makes him love her even more.

He kisses her.

She reciprocates the kiss and his heart soars until seconds later when her lips are replaced by Chuck's fist.

* * *

><p><em>Fourth time, I said that's it<br>You've agreed to give me everything  
>Now I've got to ask you one thing<br>Keep doing that forever_

_XXX  
><em>

It takes Nate and Serena to restrain Chuck and Blair looks broken and confused through the madness.

Dan remains on the floor and watches as Blair reaches for Chuck, pleads with him to talk to her, to understand, as Nate and Serena stand by his side.

It takes Raina moving past the previous fab four and offering her hand for him to get off the floor.

He walks away with heavy steps and an even heavier heart.

She catches him up to him before he exits the glitzy building and shoves him with all her might.

"What the hell was that? You just left me in there to deal with all their questions, their opinions?"

The anger in her words stings more than her shove.

"I thought..."

She bristles her lips. "You are an idiot."

He gets it then. She chose him.

It hurts to smile but he can't keep the movement from occurring.

He reaches out to her and kisses her for the second time that night. When she pulls away from him briefly to touch the bruise already forming on his face, all he wants to do is mold her lips back to his.

He could kiss her forever, he thinks.

* * *

><p><em>Fifth time in your bedroom<br>And finally, we rested  
>And you leaned upon your elbow<br>And began to speak to me_

But you stopped yourself and kissed me  
>And I grabbed your lips and told you<br>I know, I know, I know  
>I feel the same as you<p>

XXX

They are laying in her bed, her head against his chest, his fingers in her hair.

Neither has said much in the aftermath of the night. They haven't talked about them kissing in front of their friends, Blair choosing him over all of them, to where it led them: naked in each others arms in her bed.

She pulls out of his arms and brings herself up so that she is leaning over his face.

He knows what he wants to say. Three little words that almost escaped his mouth in climax. He held them back then and he holds them back now.

He opts for a different set of three words. "You are beautiful."

The blush is immediate and she smiles shyly. "Dan, I-"

His heart accelerates as he tries to guess what she might say.

She shakes her head. "Never mind."

He brings her head back to face him and looks at her eyes. Reading the doubt there, he answers her unvoiced question. "This, you and me, this is real."

She nods and presses her lips to his briefly before nestling into his arms again. "Yeah, it is," she says into his chest.

He can't fight the words anymore and they escape him. "I love you."

She stiffens for a second and he holds his breath until she moves even closer to him.

He brings his arm down to close around her body and she kisses his chest.

She doesn't say the words back but he does not need her to.

He gets it. There is no going back, no more pretending.

His world as he knew it has ended. It is her and him now.

* * *

><p><em>And everyday, it's changed since then<br>In every way, I've changed since then  
>And everyday, it's changed since then<br>In every way, I've changed since then_


End file.
